EP1392259A2 - Delivery of erectile dysfunction drugs through an inhalation route - Google Patents
Delivery of erectile dysfunction drugs through an inhalation routeInfo
- Publication number
- EP1392259A2 EP1392259A2 EP02737132A EP02737132A EP1392259A2 EP 1392259 A2 EP1392259 A2 EP 1392259A2 EP 02737132 A EP02737132 A EP 02737132A EP 02737132 A EP02737132 A EP 02737132A EP 1392259 A2 EP1392259 A2 EP 1392259A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- aerosol
- percent
- particles
- weight
- sildenafil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24V—COLLECTION, PRODUCTION OR USE OF HEAT NOT OTHERWISE PROVIDED FOR
- F24V30/00—Apparatus or devices using heat produced by exothermal chemical reactions other than combustion
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M11/00—Sprayers or atomisers specially adapted for therapeutic purposes
- A61M11/04—Sprayers or atomisers specially adapted for therapeutic purposes operated by the vapour pressure of the liquid to be sprayed or atomised
- A61M11/041—Sprayers or atomisers specially adapted for therapeutic purposes operated by the vapour pressure of the liquid to be sprayed or atomised using heaters
- A61M11/042—Sprayers or atomisers specially adapted for therapeutic purposes operated by the vapour pressure of the liquid to be sprayed or atomised using heaters electrical
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M2205/00—General characteristics of the apparatus
- A61M2205/82—Internal energy supply devices
- A61M2205/8206—Internal energy supply devices battery-operated
Definitions
- the present invention relates to the delivery of erectile dysfunction drugs through an inhalation route. Specifically, it relates to aerosols containing erectile dysfunction drugs that are used in inhalation therapy.
- compositions currently marketed for the treatment of erectile dysfunction contain at least one active ingredient that provides for observed therapeutic effects.
- active ingredients given in such erectile dysfunction compositions are sildenafil, tadalafil and vardenafil.
- the present invention relates to the delivery of erectile dysfunction drugs through an inhalation route. Specifically, it relates to aerosols containing erectile dysfunction drugs that are used in inhalation therapy. [0006]
- the aerosol comprises particles comprising at least 5 percent by weight of an erectile dysfunction drug.
- the particles comprise at least 10 percent by weight of an erectile dysfunction drug. More preferably, the particles comprise at least 20 percent, 30 percent, 40 percent, 50 percent, 60 percent, 70 percent, 80 percent, 90 percent, 95 percent, 97 percent, 99 percent, 99.5 percent or 99.97 percent by weight of an erectile dysfunction drug.
- the erectile dysfunction drug is not sildenafil citrate.
- the aerosol has a mass of at least 10 ⁇ g.
- the aerosol has a mass of at least 100 ⁇ g. More preferably, the aerosol has a mass of at least 200 ⁇ g.
- the particles comprise less than 10 percent by weight of erectile dysfunction drug degradation products.
- the particles comprise less than 5 percent by weight of erectile dysfunction drug degradation products.
- the particles comprise less than 2.5, 1, 0.5, 0.1 or 0.03 percent by weight of erectile dysfunction drug degradation products.
- the particles comprise less than 90 percent by weight of water.
- the particles comprise less than 80 percent by weight of water.
- the particles comprise less than 70 percent, 60 percent, 50 percent, 40 percent, 30 percent, 20 percent, 10 percent, or 5 percent by weight of water.
- At least 50 percent by weight of the aerosol is amorphous in form, wherein crystalline forms make up less than 50 percent by weight of the total aerosol weight, regardless of the nature of individual particles.
- at least 75 percent by weight of the aerosol is amorphous in form. More preferably, at least 90 percent by weight of the aerosol is amorphous in form.
- the aerosol has an inhalable aerosol particle density greater than 10 particles/mL.
- the aerosol has an inhalable aerosol particle density greater than 10 7 particles/mL or 10 8 particles/mL.
- the aerosol particles have a mass median aerodynamic diameter of less than 5 microns.
- the particles have a mass median aerodynamic diameter of less than 3 microns. More preferably, the particles have a mass median aerodynamic diameter of less than 2 or 1 micron(s).
- the geometric standard deviation around the mass median aerodynamic diameter of the aerosol particles is less than 3.5.
- the geometric standard deviation is less than 3.0. More preferably, the geometric standard deviation is less than 2.5 or 2.2.
- the aerosol is formed by heating a composition containing an erectile dysfunction drug to form a vapor and subsequently allowing the vapor to condense into an aerosol.
- the aerosol comprises particles comprising at least 5 percent by weight of sildenafil, tadalafil or vardenafil.
- the particles comprise at least 10 percent by weight of sildenafil, tadalafil or vardenafil. More preferably, the particles comprise at least
- sildenafil 90 percent, 95 percent, 97 percent, 99 percent, 99.5 percent or 99.97 percent by weight of sildenafil, tadalafil or vardenafil.
- the aerosol has a mass of at least 10 ⁇ g.
- the aerosol has a mass of at least 100 ⁇ g. More preferably, the aerosol has a mass of at least 200 ⁇ g.
- the particles comprise less than 10 percent by weight of sildenafil, tadalafil or vardenafil degradation products.
- the particles comprise less than 5 percent by weight of sildenafil, tadalafil or vardenafil degradation products. More preferably, the particles comprise less than 2.5, 1,
- sildenafil, tadalafil or vardenafil degradation products 0.5, 0.1 or 0.03 percent by weight of sildenafil, tadalafil or vardenafil degradation products.
- the particles comprise less than 90 percent by weight of water.
- the particles comprise less than 80 percent by weight of water.
- the particles comprise less than 70 percent, 60 percent, 50 percent, 40 percent, 30 percent, 20 percent, 10 percent, or 5 percent by weight of water.
- at least 50 percent by weight of the aerosol is amorphous in form, wherein crystalline forms make up less than 50 percent by weight of the total aerosol weight, regardless of the nature of individual particles.
- at least 75 percent by weight of the aerosol is amorphous in form. More preferably, at least 90 percent by weight of the aerosol is amorphous in form.
- the aerosol has an inhalable aerosol drug mass density of between 5 mg/L and 40 mg/L.
- the aerosol has an inhalable aerosol drug mass density of between 10 mg/L and 35 mg/L. More preferably, the aerosol has an inhalable aerosol drug mass density of between 15 mg/L and 30 mg/L.
- the aerosol comprises tadalafil
- the aerosol has an inhalable aerosol drug mass density of between 2.5 mg/L and 20 mg/L.
- the aerosol has an inhalable aerosol drug mass density of between 3.5 mg/L and 17.5 mg/L. More preferably, the aerosol has an inhalable aerosol drug mass density of between 5 mg/L and 15 mg/L.
- the aerosol has an inhalable aerosol drug mass density of between 1 mg/L and 20 mg/L.
- the aerosol has an inhalable aerosol drug mass density of between 1.5 mg/L and
- the aerosol has an inhalable aerosol drug mass density of between 2 mg/L and 15 mg/L.
- the aerosol has an inhalable aerosol particle density greater than 10 particles/mL.
- the aerosol has an inhalable aerosol particle density greater than 10 7 particles/mL or 10 8 particles/mL.
- the aerosol particles have a mass median aerodynamic diameter of less than 5 microns.
- the particles have a mass median aerodynamic diameter of less than 3 microns. More preferably, the particles have a mass median aerodynamic diameter of less than 2 or 1 micron(s).
- the geometric standard deviation around the mass median aerodynamic diameter of the aerosol particles is less than 3.5.
- the geometric standard deviation is less than 3.0. More preferably, the geometric standard deviation is less than 2.5 or 2.2.
- the aerosol is formed by heating a composition containing sildenafil, tadalafil or vardenafil to form a vapor and subsequently allowing the vapor to condense into an aerosol.
- an erectile dysfunction drug is delivered to a mammal through an inhalation route.
- the method comprises: a) heating a composition, wherein the composition comprises at least 5 percent by weight of an erectile dysfunction drug, to form a vapor; and, b) allowing the vapor to cool, thereby forming a condensation aerosol comprising particles, which is inhaled by the mammal.
- the composition that is heated comprises at least 10 percent by weight of an erectile dysfunction drug.
- the composition comprises at least 20 percent, 30 percent, 40 percent, 50 percent, 60 percent, 70 percent, 80 percent, 90 percent, 95 percent, 97 percent, 99 percent, 99.5 percent, 99.9 percent or 99.97 percent by weight of an erectile dysfunction drug.
- the particles comprise at least 5 percent by weight of an erectile dysfunction drug.
- the particles comprise at least 10 percent by weight of an erectile dysfunction drug. More preferably, the particles comprise at least 20 percent, 30 percent, 40 percent, 50 percent, 60 percent, 70 percent, 80 percent, 90 percent, 95 percent, 97 percent, 99 percent, 99.5 percent, 99.9 percent or 99.97 percent by weight of an erectile dysfunction drug.
- the aerosol has a mass of at least 10 ⁇ g.
- the aerosol has a mass of at least 100 ⁇ g. More preferably, the aerosol has a mass of at least 200 ⁇ g.
- the particles comprise less than 10 percent by weight of erectile dysfunction drug degradation products.
- the particles comprise less than 5 percent by weight of erectile dysfunction drug degradation products. More preferably, the particles comprise 2.5, 1, 0.5, 0.1 or 0.03 percent by weight of erectile dysfunction drug degradation products.
- the particles comprise less than 90 percent by weight of water.
- the particles comprise less than 80 percent by weight of water. More preferably, the particles comprise less than 70 percent, 60 percent, 50 percent, 40 percent, 30 percent, 20 percent, 10 percent, or 5 percent by weight of water.
- At least 50 percent by weight of the aerosol is amorphous in form, wherein crystalline forms make up less than 50 percent by weight of the total aerosol weight, regardless of the nature of individual particles.
- at least 75 percent by weight of the aerosol is amorphous in form. More preferably, at least 90 percent by weight of the aerosol is amorphous in form.
- the particles of the delivered condensation aerosol have a mass median aerodynamic diameter of less than 5 microns.
- the particles have a mass median aerodynamic diameter of less than 3 microns. More preferably, the particles have a mass median aerodynamic diameter of less than 2 or 1 micron(s).
- the geometric standard deviation around the mass median aerodynamic diameter of the aerosol particles is less than 3.5.
- the geometric standard deviation is less than 3.0. More preferably, the geometric standard deviation is less than 2.5 or 2.2.
- the delivered aerosol has an inhalable aerosol particle density greater than 10 6 particles/mL.
- the aerosol has an inhalable aerosol particle density greater than 10 particles/mL or 10 particles/mL.
- the rate of inhalable aerosol particle formation of the delivered condensation aerosol is greater than 10 8 particles per second.
- the aerosol is formed at a rate greater than 10 9 inhalable particles per second. More preferably, the aerosol is formed at a rate greater than 10 10 inhalable particles per second.
- the delivered condensation aerosol is formed at a rate greater than 0.5 mg/second.
- the aerosol is formed at a rate greater than 0.75 mg/second. More preferably, the aerosol is formed at a rate greater than
- the delivered condensation aerosol results in a peak plasma concentration of an erectile dysfunction drug in the mammal in less than 1 h.
- the peak plasma concentration is reached in less than 0.5 h. More preferably, the peak plasma concentration is reached in less than 0.2, 0.1, 0.05, 0.02, 0.01, or 0.005 h (arterial measurement).
- sildenafil, tadalafil or vardenafil is delivered to a mammal through an inhalation route.
- the method comprises: a) heating a composition, wherein the composition comprises at least 5 percent by weight of sildenafil, tadalafil or vardenafil, to form a vapor; and, b) allowing the vapor to cool, thereby forming a condensation aerosol comprising particles, which is inhaled by the mammal.
- the composition that is heated comprises at least 10 percent by weight of sildenafil, . tadalafil or vardenafil.
- the composition comprises at least 20 percent, 30 percent, 40 percent, 50 percent, 60 percent, 70 percent, 80 percent, 90 percent, 95 percent, 97 percent, 99 percent, 99.5 percent, 99.9 percent or 99.97 percent by weight of sildenafil, tadalafil or vardenafil.
- the particles comprise at least 5 percent by weight of sildenafil, tadalafil or vardenafil.
- the particles comprise at least 10 percent by weight of sildenafil, tadalafil or vardenafil.
- the particles comprise at least 20 percent, 30 percent, 40 percent, 50 percent, 60 percent, 70 percent, 80 percent, 90 percent, 95 percent, 97 percent, 99 percent, 99.5 percent, 99.9 percent or 99.97 percent by weight of sildenafil, tadalafil or vardenafil.
- the aerosol has a mass of at least 10 ⁇ g.
- the aerosol has a mass of at least 100 ⁇ g. More preferably, the aerosol has a mass of at least 200 ⁇ g.
- the particles comprise less than 10 percent by weight of sildenafil, tadalafil or vardenafil degradation products.
- the particles comprise less than 5 percent by weight of sildenafil, tadalafil or vardenafil degradation products. More preferably, the particles comprise 2.5, 1, 0.5, 0.1 or 0.03 percent by weight of sildenafil, tadalafil or vardenafil degradation products.
- the particles comprise less than 90 percent by weight of water.
- the particles comprise less than 80 percent by weight of water. More preferably, the particles comprise less than 70 percent, 60 percent, 50 percent, 40 percent, 30 percent, 20 percent, 10 percent, or 5 percent by weight of water.
- At least 50 percent by weight of the aerosol is amorphous in form, wherein crystalline forms make up less than 50 percent by weight of the total aerosol weight, regardless of the nature of individual particles.
- at least 75 percent by weight of the aerosol is amorphous in form. More preferably, at least 90 percent by weight of the aerosol is amorphous in form.
- the particles of the delivered condensation aerosol have a mass median aerodynamic diameter of less than 5 microns.
- the particles have a mass median aerodynamic diameter of less than 3 microns. More preferably, the particles have a mass median aerodynamic diameter of less than 2 or 1 micron(s).
- the geometric standard deviation around the mass median aerodynamic diameter of the aerosol particles is less than 3.5.
- the geometric standard deviation is less than 3.0. More preferably, the geometric standard deviation is less than 2.5 or 2.2.
- the delivered aerosol has an inhalable aerosol drug mass density of between 5 mg/L and 40 mg/L.
- the aerosol has an inhalable aerosol drug mass density of between 10 mg/L and 35 mg/L. More preferably, the aerosol has an inhalable aerosol drug mass density of between 15 mg/L and 30 mg/L.
- the delivered aerosol has an inhalable aerosol drug mass density of between 2.5 mg/L and 20 mg/L.
- the aerosol has an inhalable aerosol drug mass density of between 3.5 mg/L and 17.5 mg/L. More preferably, the aerosol has an inhalable aerosol drug mass density of between 5 mg/L and 15 mg/L.
- the delivered aerosol has an inhalable aerosol drag mass density of between 1 mg/L and 20 mg/L.
- the aerosol has an inhalable aerosol drug mass density of between 1.5 mg/L and 17.5 mg/L. More preferably, the aerosol has an inhalable aerosol drug mass density of between 2 mg/L and 15 mg/L.
- the delivered aerosol has an inhalable aerosol particle density greater than 10 6 particles/mL.
- the aerosol has an inhalable aerosol particle density greater than 10 7 particles/mL or 10 8 particles/mL.
- the rate of inhalable aerosol particle formation of the delivered condensation aerosol is greater than 10 particles per second.
- the aerosol is formed at a rate greater than 10 9 inhalable particles per second. More preferably, the aerosol is formed at a rate greater than 10 10 inhalable particles per second.
- the delivered condensation aerosol is formed at a rate greater than 0.5 mg/second.
- the aerosol is formed at a rate greater than 0.75 mg/second. More preferably, the aerosol is formed at a rate greater than 1 mg/second, 1.5 mg/second or 2 mg/second.
- the condensation aerosol comprises sildenafil
- between 5 mg and 40 mg of sildenafil are delivered to the mammal in a single inspiration.
- the condensation aerosol comprises tadalafil
- tadalafil between 2.5 mg and 20 mg of tadalafil are delivered to the mammal in a single inspiration.
- tadalafil preferably, between 3.5 mg and 17.5 mg of tadalafil are delivered to the mammal in a single inspiration. More preferably, between 5 mg and 15 mg of tadalafil are delivered in a single inspiration.
- the condensation aerosol comprises vardenafil
- between 1 mg and 20 mg of vardenafil are delivered to the mammal in a single inspiration.
- the delivered condensation aerosol results in a peak plasma concentration of sildenafil, tadalafil or vardenafil in the mammal in less than 1 h.
- the peak plasma concentration is reached in less than 0.5 h. More preferably, the peak plasma concentration is reached in less than 0.2, 0.1, 0.05, 0.02, 0.01, or 0.005 h (arterial measurement).
- kits for delivering an erectile dysfunction drug through an inhalation route to a mammal which comprises: a) a composition comprising at least 5 percent by weight of an erectile dysfunction drug; and, b) a device that forms an erectile dysfunction drug aerosol from the composition, for inhalation by the mammal.
- the composition comprises at least 20 percent, 30 percent, 40 percent, 50 percent, 60 percent, 70 percent, 80 percent, 90 percent, 95 percent, 97 percent, 99 percent, 99.5 percent, 99.9 percent or 99.97 percent by weight of an erectile dysfunction drug.
- the device contained in the kit comprises: a) an element for heating the erectile dysfunction drug composition to form a vapor; b) an element , allowing the vapor to cool to form an aerosol; and, c) an element permitting the mammal to inhale the aerosol.
- kits for delivering sildenafil, tadalafil or vardenafil through an inhalation route to a mammal which comprises: a) a composition comprising at least 5 percent by weight of sildenafil, tadalafil or vardenafil; and, b) a device that forms a sildenafil, tadalafil or vardenafil aerosol from the composition, for inhalation by the mammal.
- the composition comprises at least 20 percent, 30 percent, 40 percent, 50 percent, 60 percent, 70 percent, 80 percent, 90 percent, 95 percent, 97 percent, 99 percent, 99.5 percent, 99.9 percent or 99.97 percent by weight of sildenafil, tadalafil or vardenafil.
- the device contained in the kit comprises: a) an element for heating the sildenafil, tadalafil or vardenafil composition to form a vapor; b) an element allowing the vapor to cool to form an aerosol; and, c) an element permitting the mammal to inhale the aerosol.
- Fig. 1 shows a cross-sectional view of a device used to deliver erectile dysfunction drug aerosols to a mammal through an inhalation route.
- Aerodynamic diameter of a given particle refers to the diameter of a spherical droplet with a density of 1 g/mL (the density of water) that has the same settling velocity as the given particle.
- Alcohol refers to a suspension of solid or liquid particles in a gas.
- Aerosol drug mass density refers to the mass of sildenafil or tadalafil per unit volume of aerosol.
- Aerosol mass density refers to the mass of particulate matter per unit volume of aerosol.
- Aerosol particle density refers to the number of particles per unit volume of aerosol.
- Amorphous particle refers to a particle that does not contain more than 50 percent by weight of a crystalline form. Preferably, the particle does not contain more than 25 percent by weight of a crystalline form. More preferably, the particle does not contain more than 10 percent by weight of a crystalline form.
- Condensation aerosol refers to an aerosol formed by vaporization of a substance followed by condensation of the substance into an aerosol.
- Erectile dysfunction drug degradation product refers to a compound resulting from a chemical modification of an erectile dysfunction drug.
- the modification for example, can be the result of a thermally or photochemically induced reaction. Such reactions include, without limitation, oxidation and hydrolysis.
- Inhalable aerosol drug mass density refers to the aerosol drug mass density produced by an inhalation device and delivered into a typical patient tidal volume.
- “Inhalable aerosol mass density” refers to the aerosol mass density produced by an inhalation device and delivered into a typical patient tidal volume.
- Inhalable aerosol particle density refers to the aerosol particle density of particles of size between 100 nm and 5 microns produced by an inhalation device and delivered into a typical patient tidal volume.
- Mass median aerodynamic diameter or “MMAD” of an aerosol refers to the aerodynamic diameter for which half the particulate mass of the aerosol is contributed by particles with an aerodynamic diameter larger than the
- Rate of aerosol formation refers to the mass of aerosolized particulate matter produced by an inhalation device per unit time.
- Rate of inhalable aerosol particle formation refers to the number of particles of size between 100 nm and 5 microns produced by an inhalation device per unit time.
- Rate of drug aerosol formation refers to the mass of aerosolized sildenafil or tadalafil produced by an inhalation device per unit time.
- Settling velocity refers to the terminal velocity of an aerosol particle undergoing gravitational settling in air.
- “Sildenafil” refers to 5- [2-ethoxy-5-(4-methylpiperazin- 1 - ylsulfonyl)phenyl] - 1 - methyl-3 -propyl- 1 ,6-dihy dro-7H-pyrazolo [4,3 -djpyrimidin-
- Silicondenafil degradation product refers to a compound resulting from a chemical modification of sildenafil.
- the modification for example, can be the result of a thermally or photochemically induced reaction. Such reactions include, without limitation, oxidation and hydrolysis.
- Tadalafil refers to (6R, 12aR)-2,3, 6,7, 12,12a-hexal ydro-2-methyl-6-
- Tadalafil degradation product refers to a compound resulting from a chemical modification of tadalafil.
- the modification for example, can be the result of a thermally or photochemically induced reaction.
- Such reactions include, without limitation, oxidation and hydrolysis.
- Typical patient tidal volume refers to 1 L for an adult patient and 15 mL/kg for a pediatric patient.
- Vapor refers to a gas
- vapor phase refers to a gas phase
- thermal vapor refers to a vapor phase, aerosol, or mixture of aerosol- vapor phases, formed preferably by heating.
- Vardenafil refers to l-[[3-(l,4-dihydro-5-methyl-4-oxo-7- propylimidazo[5, 1 -fj [1 ,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethyl- piperazine (C 23 H 32 N 6 O 4 S).
- Vardenafil degradation product refers to a compound resulting from a chemical modification of vardenafil.
- the modification for example, can be the result of a thermally or photochemically induced reaction. Such reactions include, without limitation, oxidation and hydrolysis.
- any suitable method is used to form the aerosols of the present invention.
- a preferred method involves heating a composition comprising an erectile dysfunction drug to form a vapor, followed by cooling of the vapor such that it condenses to provide an erectile dysfunction drug comprising aerosol (condensation aerosol).
- the composition is heated in one of four forms: as pure active compound (e.g., pure sildenafil, tadalafil or vardenafil); as a mixture of active compound and a pharmaceutically acceptable excipient; as a salt form of the pure active compound; and, as a mixture of active compound salt form and a pharmaceutically acceptable excipient.
- Salt forms of erectile dysfunction drugs are either commercially available or are obtained from the corresponding free base using well known methods in the art.
- a variety of pharmaceutically acceptable salts are suitable for aerosolization. Such salts include, without limitation, the following: hydrochloric acid, hydrobromic acid, acetic acid, maleic acid, formic acid, and fumaric acid salts.
- Pharmaceutically acceptable excipients may be volatile or nonvolatile. Volatile excipients, when heated, are concurrently volatilized, aerosolized and inhaled with the erectile dysfunction drug.
- Classes of such excipients include, without limitation, gaseous, supercritical fluid, liquid and solid solvents.
- the following is a list of exemplary carriers within the classes: water; terpenes, such as menthol; alcohols, such as ethanol, propylene glycol, glycerol and other similar alcohols; dimethylformamide; dimethylacetamide; wax; supercritical carbon dioxide; dry ice; and mixtures thereof.
- Solid supports on which the composition is heated are of a variety of shapes. Examples of such shapes include, without limitation, cylinders of less than 1.0 mm in diameter, boxes of less than 1.0 mm thickness and virtually any shape permeated by small (e.g., less than 1.0 mm-sized) pores.
- solid supports provide a large surface to volume ratio (e.g., greater than 100 per meter) and a large surface to mass ratio (e.g., greater than 1 cm 2 per gram).
- a solid support of one shape can also be transformed into another shape with different properties. For example, a flat sheet of 0.25 mm thickness has a surface to volume ratio of approximately 8,000 per meter. Rolling the sheet into a hollow cylinder of 1 cm diameter produces a support that retains the high surface to mass ratio of the original sheet but has a lower surface to volume ratio (about 400 per meter).
- a number of different materials are used to construct the solid supports. Classes of such materials include, without limitation, metals, inorganic materials, carbonaceous materials and polymers. The following are examples of the material classes: aluminum, silver, gold, stainless steel, copper and tungsten; silica, glass, silicon and alumina; graphite, porous carbons, carbon yarns and carbon felts; polytetrafluoroethylene and polyethylene glycol. Combinations of materials and coated variants of materials are used as well. [0093] Where aluminum is used as a solid support, aluminum foil is a suitable material. Examples of silica, alumina and silicon based materials include amphorous silica S-5631 (Sigma, St.
- the heating of the erectile drug compositions is performed using any suitable method.
- methods by which heat can be generated include the following: passage of current through an electrical resistance element; absorption of electromagnetic radiation, such as microwave or laser light; and, exothermic chemical reactions, such as exothermic solvation, hydration of pyrophoric materials and oxidation of combustible materials.
- Erectile dysfunction drug containing aerosols of the present invention are delivered to a mammal using an inhalation device.
- the aerosol is a condensation aerosol
- the device has at least three elements: an element for heating an erectile dysfunction drag containing composition to form a vapor; an element allowing the vapor to cool, thereby providing a condensation aerosol; and, an element permitting the mammal to inhale the aerosol.
- Various suitable heating methods are described above.
- the element that allows cooling is, in it simplest form, an inert passageway linking the heating means to the inhalation means.
- the element permitting inhalation is an aerosol exit portal that forms a connection between the cooling element and the mammal's respiratory system.
- Delivery device 100 has a proximal end 102 and a distal end 104, a heating module 106, a power source 108, and a mouthpiece 110.
- An erectile dysfunction drug composition is deposited on a surface 112 of heating module 106.
- power source 108 initiates heating of heating module 106 (e.g, through ignition of combustible fuel or passage of current through a resistive heating element).
- the erectile dysfunction drug composition volatilizes due to the heating of heating module 106 and condenses to form a condensation aerosol prior to reaching the mouthpiece 110 at the proximal end of the device 102. Air flow traveling from the device distal end 104 to the mouthpiece 110 carries the condensation aerosol to the mouthpiece 110, where it is inhaled by the mammal.
- Devices if desired, contain a variety of components to facilitate the delivery of erectile dysfunction drag containing aerosols.
- the device may include any component known in the art to control the timing of drug aerosolization relative to inhalation (e.g., breath-actuation), to provide feedback to patients on the rate and/or volume of inhalation, to prevent excessive use (i.e., "lock-out” feature), to prevent use by unauthorized individuals, and/or to record dosing histories.
- breath-actuation e.g., breath-actuation
- lock-out i.e., "lock-out” feature
- the dosage amount of an erectile dysfunction drug in aerosol form is generally no greater than twice the standard dose of the drug given orally.
- sildenafil, tadalafil and vardenafil are given at strengths of 25 mg, 10 mg, and 5 mg respectively for the treatment of erectile dysfunction.
- 5 mg to 40 mg of sildenafil, 2.5 mg to 20 mg of tadalafil, and 1 to 20 mg of vardenafil are generally provided for the same indication.
- a typical dosage of an erectile dysfunction drag aerosol is either administered as a single inhalation or as a series of inhalations taken within an hour or less (dosage equals sum of inhaled amounts). Where the drug is administered as a series of inhalations, a different amount may be delivered in each inhalation.
- One animal experiment involves measuring plasma concentrations of drug in an animal after its exposure to the aerosol. Mammals such as dogs or primates are typically used in such studies, since their respiratory systems are similar to that of a human.
- Initial dose levels for testing in humans is generally less than or equal to the dose in the mammal model that resulted in plasma drag levels associated with a therapeutic effect in humans. Dose escalation in humans is then performed, until either an optimal therapeutic response is obtained or a dose-limiting toxicity is encountered.
- erectile dysfunction drag containing aerosol is determined using a number of methods, examples of which are described in Sekine et al., Journal of Forensic Science 32:1271-1280 (1987) and Martin et al, Journal of Analytic Toxicology 13:158-162 (1989).
- One method involves forming the aerosol in a device through which a gas flow (e.g., air flow) is maintained, generally at a rate between 0.4 and 60 L/min.
- the gas flow carries the aerosol into one or more traps.
- the aerosol is subjected to an analytical technique, such as gas or liquid chromatography, that permits a determination of composition purity.
- a variety of different traps are used for aerosol collection.
- the following list contains examples of such traps: filters; glass wool; impingers; solvent traps, such as dry ice-cooled ethanol, methanol, acetone and dichloromethane traps at various pH values; syringes that sample the aerosol; empty, low-pressure (e.g., vacuum) containers into which the aerosol is drawn; and, empty containers that fully surround and enclose the aerosol generating device.
- a solid such as glass wool
- it is typically extracted with a solvent such as ethanol.
- the solvent extract is subjected to analysis rather than the solid (i.e., glass wool) itself.
- the container is similarly extracted with a solvent.
- the gas or liquid chromatograph discussed above contains a detection system (i.e., detector).
- detection systems are well known in the art and include, for example, flame ionization, photon absorption and mass spectrometry detectors.
- An advantage of a mass spectrometry detector is that it can be used to determine the structure of erectile dysfunction drag degradation products.
- Particle size distribution of an erectile dysfunction drug containing aerosol is determined using any suitable method in the art (e.g., cascade impaction).
- An Andersen Eight Stage Non-viable Cascade Impactor (Andersen Instruments, Smyrna, GA) linked to a furnace tube by a mock throat (USP throat, Andersen Instruments, Smyrna, GA) is one system used for cascade impaction studies.
- Inhalable aerosol mass density is determined, for example, by delivering a drag-containing aerosol into a confined chamber via an inhalation device and measuring the mass collected in the chamber.
- the aerosol is drawn into the chamber by having a pressure gradient between the device and the chamber, wherein the chamber is at lower pressure than the device.
- the volume of the chamber should approximate the tidal volume of an inhaling patient.
- Inhalable aerosol drug mass density is determined, for example, by delivering a drag-containing aerosol into a confined chamber via an inhalation device and measuring the amount of active drug compound collected in the chamber.
- the aerosol is drawn into the chamber by having a pressure gradient between the device and the chamber, wherein the chamber is at lower pressure than the device.
- the volume of the chamber should approximate the tidal volume of an inhaling patient.
- the amount of active drug compound collected in the chamber is determined by extracting the chamber, conducting chromatographic analysis of the extract and comparing the results of the chromatographic analysis to those of a standard containing known amounts of drag.
- Inhalable aerosol particle density is determined, for example, by delivering aerosol phase drag into a confined chamber via an inhalation device and measuring the number of particles of given size collected in the chamber.
- the number of particles of a given size may be directly measured based on the light-scattering properties of the particles.
- Number of particles in a given size range Mass in the size range/Mass of a typical particle in the size range.
- Mass of a typical particle in a given size range ⁇ *D 3 * ⁇ /6, where D is a typical particle diameter in the size range (generally, the mean boundary MMADs defining the size range) in microns, ⁇ is the particle density (in g/mL) and mass is given in units of picograms (g "12 ).
- Rate of inhalable aerosol particle formation is determined, for example, by delivering aerosol phase drag into a confined chamber via an inhalation device. The delivery is for a set period of time (e.g., 3 s), and the number of particles of a given size collected in the chamber is determined as outlined above. The rate of particle formation is equal to the number of 100 nm to 5 micron particles collected divided by the duration of the collection time. [0108] Rate of aerosol formation is determined, for example, by delivering aerosol phase drug into a confined chamber via an inhalation device.
- the delivery is for a set period of time (e.g., 3 s), and the mass of particulate matter collected is determined by weighing the confined chamber before and after the delivery of the particulate matter.
- the rate of aerosol formation is equal to the increase in mass in the chamber divided by the duration of the collection time.
- the mass of particulate matter may be equated with the mass lost from the device or component during the delivery of the aerosol.
- the rate of aerosol formation is equal to the decrease in mass of the device or component during the delivery event divided by the duration of the delivery event.
- Rate of drug aerosol formation is determined, for example, by delivering an erectile dysfunction drug containing aerosol into a confined chamber via an inhalation device over a set period of time (e.g., 3 s). Where the aerosol is pure erectile dysfunction drag, the amount of drag collected in the chamber is measured as described above. The rate of -drug aerosol formation is equal to the amount of erectile dysfunction drug collected in the chamber divided by the duration of the collection time. Where the erectile dysfunction drug containing aerosol comprises a pharmaceutically acceptable excipient, multiplying the rate of aerosol formation by the percentage of erectile dysfunction drug in the aerosol provides the rate of drug aerosol formation.
- the erectile dysfunction drug containing aerosols of the present invention are typically used for the treatment of erectile dysfunction.
- Tadalafil can be synthesized using the methods described in U.S. Pat. No. 6,143,746 (issued
- Vardenafil can be synthesized using the methods described in WO/99/24433 (published May 20,
- salt e.g., mono hydrochloride
- deionized water ⁇ 30 mL
- three equivalents of sodium hydroxide I N NaOH aq
- the aqueous solution is extracted four times with dichloromethane ( ⁇ 50 mL), and the extracts are combined, dried (Na SO 4 ) and filtered.
- the filtered organic solution is concentrated using a rotary evaporator to provide the desired free base. If necessary, purification of the free base is performed using standard methods such as chromatography or recrystallization.
- a solution of drag in approximately 120 ⁇ L dichloromethane is coated on a 3.5 cm x 7.5 cm piece of aluminum foil (precleaned with acetone). The dichloromethane is allowed to evaporate. The coated foil is wrapped around a 300 watt halogen tube (Feit Electric Company, Pico Rivera, CA), which is inserted into a glass tube sealed at one end with a rubber stopper. Running 90 V of alternating current (driven by line power controlled by a variac) through the bulb for 2.5 s affords thermal vapor (including aerosol), which is collected on the glass tube walls. Reverse-phase HPLC analysis with detection by absorption of 225 nm light is used to determine the purity of the aerosol.
- Tadalafil aerosol (0.29 mg) was obtained in 98.5% purity using this procedure. To obtain higher purity aerosols, one can coat a lesser amount of drug, yielding a thinner film to heat. A linear decrease in film thickness is associated with a linear decrease in impurities.
- a flash assembly consisting of a stainless steel outer cylinder and an inner brass electrode was dipped into an organic solution containing a drug and quickly removed. Evaporation of residual solvent from the assembly was performed by air drying. This left a film of drag coated on the exterior surface of the stainless steel cylinder.
- the assembly was electrically connected to a capacitor network (e.g., 1.5 F) and a mechanical relay using brass connectors and then placed into a glass sleeve.
- a filter assembly was placed between the glass sleeve and a vacuum system. Flow ( ⁇ 15 L/min) was instigated through the glass sleeve using the vacuum system.
- Heating of the flash assembly was performed for about 0.25 s by momentarily turning on the relay between the flash assembly and the capacitors (connected to DC power supply and charged to 20.5 V) to volatilize (form an aerosol of) the coated drug.
- the assembly was allowed to cool.
- Analysis of the formed aerosol involved rinsing the filter with 5 mL of acetonitrile and injecting a sample of the organic solution into an HPLC.
- Sildenafil aerosol was obtained in 98.9% purity (0.075 mg) using this procedure.
- Vardenafil aerosol was obtained in 81.4% purity (0.7 mg) using this procedure.
Abstract
Description
Claims
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US29420301P | 2001-05-24 | 2001-05-24 | |
US294203P | 2001-05-24 | ||
US31747901P | 2001-09-05 | 2001-09-05 | |
US317479P | 2001-09-05 | ||
PCT/US2002/016398 WO2002094219A2 (en) | 2001-05-24 | 2002-05-22 | Delivery of erectile dysfunction drugs through an inhalation route |
Publications (2)
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EP1392259A2 true EP1392259A2 (en) | 2004-03-03 |
EP1392259B1 EP1392259B1 (en) | 2007-06-27 |
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EP02741994A Withdrawn EP1392262A1 (en) | 2001-05-24 | 2002-05-13 | Delivery of drug esters through an inhalation route |
EP02729255A Withdrawn EP1389095A1 (en) | 2001-05-24 | 2002-05-16 | Delivery of antidepressants through an inhalation route |
EP08014271A Expired - Lifetime EP1987823B1 (en) | 2001-05-24 | 2002-05-17 | Condensation aerosol containing zaleplon for inhalation |
EP02729235A Expired - Lifetime EP1389094B1 (en) | 2001-05-24 | 2002-05-17 | Delivery of sedative-hypnotics trough an inhalation route |
EP02771848A Expired - Lifetime EP1392264B1 (en) | 2001-05-24 | 2002-05-17 | Delivery of antiemetics through an inhalation route |
EP02731896A Expired - Lifetime EP1389097B1 (en) | 2001-05-24 | 2002-05-20 | Delivery of compounds for the treatment of parkinsons through an inhalation route |
EP02737053A Expired - Lifetime EP1389098B1 (en) | 2001-05-24 | 2002-05-20 | Delivery of antipsychotics through an inhalation route |
EP02737054A Withdrawn EP1389099A1 (en) | 2001-05-24 | 2002-05-20 | Delivery of beta-blockers through an inhalation route |
EP08014272A Expired - Lifetime EP1990046B1 (en) | 2001-05-24 | 2002-05-20 | Condensation aerosol containing loxapine or prochlorperazine for inhalation |
EP02731894A Expired - Lifetime EP1389096B9 (en) | 2001-05-24 | 2002-05-21 | Delivery of opioids through an inhalation route |
EP02731930A Expired - Lifetime EP1392257B1 (en) | 2001-05-24 | 2002-05-21 | Delivery of antihistamines through an inhalation route |
EP02737132A Expired - Lifetime EP1392259B1 (en) | 2001-05-24 | 2002-05-22 | Delivery of erectile dysfunction drugs through an inhalation route |
EP02739410A Expired - Lifetime EP1392261B1 (en) | 2001-05-24 | 2002-05-23 | Delivery of nonsteroidal antiinflammatory drugs through an inhalation route |
EP02737120A Expired - Lifetime EP1390021B1 (en) | 2001-05-24 | 2002-05-23 | Delivery of compounds for the treatment of migraine through an inhalation route |
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EP02729255A Withdrawn EP1389095A1 (en) | 2001-05-24 | 2002-05-16 | Delivery of antidepressants through an inhalation route |
EP08014271A Expired - Lifetime EP1987823B1 (en) | 2001-05-24 | 2002-05-17 | Condensation aerosol containing zaleplon for inhalation |
EP02729235A Expired - Lifetime EP1389094B1 (en) | 2001-05-24 | 2002-05-17 | Delivery of sedative-hypnotics trough an inhalation route |
EP02771848A Expired - Lifetime EP1392264B1 (en) | 2001-05-24 | 2002-05-17 | Delivery of antiemetics through an inhalation route |
EP02731896A Expired - Lifetime EP1389097B1 (en) | 2001-05-24 | 2002-05-20 | Delivery of compounds for the treatment of parkinsons through an inhalation route |
EP02737053A Expired - Lifetime EP1389098B1 (en) | 2001-05-24 | 2002-05-20 | Delivery of antipsychotics through an inhalation route |
EP02737054A Withdrawn EP1389099A1 (en) | 2001-05-24 | 2002-05-20 | Delivery of beta-blockers through an inhalation route |
EP08014272A Expired - Lifetime EP1990046B1 (en) | 2001-05-24 | 2002-05-20 | Condensation aerosol containing loxapine or prochlorperazine for inhalation |
EP02731894A Expired - Lifetime EP1389096B9 (en) | 2001-05-24 | 2002-05-21 | Delivery of opioids through an inhalation route |
EP02731930A Expired - Lifetime EP1392257B1 (en) | 2001-05-24 | 2002-05-21 | Delivery of antihistamines through an inhalation route |
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EP02739410A Expired - Lifetime EP1392261B1 (en) | 2001-05-24 | 2002-05-23 | Delivery of nonsteroidal antiinflammatory drugs through an inhalation route |
EP02737120A Expired - Lifetime EP1390021B1 (en) | 2001-05-24 | 2002-05-23 | Delivery of compounds for the treatment of migraine through an inhalation route |
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EP (14) | EP1392262A1 (en) |
JP (7) | JP2005503425A (en) |
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- 2002-05-20 JP JP2002590955A patent/JP4578773B2/en not_active Expired - Lifetime
- 2002-05-20 WO PCT/US2002/016118 patent/WO2002094236A1/en active Application Filing
- 2002-05-20 EP EP02731896A patent/EP1389097B1/en not_active Expired - Lifetime
- 2002-05-20 ES ES08014272T patent/ES2341392T3/en not_active Expired - Lifetime
- 2002-05-20 MX MXPA03010703A patent/MXPA03010703A/en active IP Right Grant
- 2002-05-20 US US10/152,639 patent/US6716416B2/en not_active Expired - Lifetime
- 2002-05-20 EP EP02737053A patent/EP1389098B1/en not_active Expired - Lifetime
- 2002-05-20 AT AT08014272T patent/ATE462421T1/en not_active IP Right Cessation
- 2002-05-20 DK DK02737053T patent/DK1389098T3/en active
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- 2002-05-20 NZ NZ529419A patent/NZ529419A/en unknown
- 2002-05-20 AT AT02731896T patent/ATE404184T1/en not_active IP Right Cessation
- 2002-05-20 US US10/153,139 patent/US6814954B2/en not_active Expired - Lifetime
- 2002-05-20 AT AT02737053T patent/ATE404173T1/en active
- 2002-05-20 DE DE60235852T patent/DE60235852D1/en not_active Expired - Lifetime
- 2002-05-20 EP EP02737054A patent/EP1389099A1/en not_active Withdrawn
- 2002-05-20 EP EP08014272A patent/EP1990046B1/en not_active Expired - Lifetime
- 2002-05-20 US US10/152,652 patent/US6740307B2/en not_active Expired - Fee Related
- 2002-05-20 US US10/152,640 patent/US6743415B2/en not_active Expired - Fee Related
- 2002-05-20 ES ES02737053T patent/ES2311607T3/en not_active Expired - Lifetime
- 2002-05-20 PT PT02737053T patent/PT1389098E/en unknown
- 2002-05-21 CA CA002446916A patent/CA2446916C/en not_active Expired - Fee Related
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- 2002-05-21 US US10/153,311 patent/US6884408B2/en not_active Expired - Fee Related
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- 2002-05-21 US US10/153,839 patent/US6776978B2/en not_active Expired - Lifetime
- 2002-05-21 NZ NZ529420A patent/NZ529420A/en unknown
- 2002-05-21 AT AT02731930T patent/ATE401063T1/en not_active IP Right Cessation
- 2002-05-21 US US10/153,831 patent/US6740308B2/en not_active Expired - Lifetime
- 2002-05-21 AT AT02731894T patent/ATE425746T1/en active
- 2002-05-21 JP JP2002590964A patent/JP2004535403A/en active Pending
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- 2002-05-21 AU AU2002303833A patent/AU2002303833B2/en not_active Ceased
- 2002-05-22 JP JP2002590938A patent/JP2004531556A/en active Pending
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- 2002-05-22 US US10/155,703 patent/US6803031B2/en not_active Expired - Fee Related
- 2002-05-22 NZ NZ529418A patent/NZ529418A/en unknown
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- 2002-05-23 US US10/154,594 patent/US6740309B2/en not_active Expired - Fee Related
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2003
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- 2003-12-12 US US10/735,199 patent/US7070761B2/en not_active Expired - Fee Related
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- 2003-12-30 US US10/749,535 patent/US7115250B2/en not_active Expired - Fee Related
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2004
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- 2004-01-27 US US10/766,634 patent/US7070763B2/en not_active Expired - Lifetime
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- 2004-01-29 US US10/769,197 patent/US7063831B2/en not_active Expired - Fee Related
- 2004-01-29 US US10/768,281 patent/US7169378B2/en not_active Expired - Lifetime
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2006
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- 2006-06-30 US US11/479,361 patent/US7524484B2/en not_active Expired - Fee Related
- 2006-06-30 US US11/479,892 patent/US7449174B2/en not_active Expired - Fee Related
- 2006-07-05 US US11/481,279 patent/US7449175B2/en not_active Expired - Fee Related
- 2006-07-18 US US11/488,932 patent/US7601337B2/en not_active Expired - Lifetime
- 2006-07-18 US US11/488,943 patent/US20060257329A1/en not_active Abandoned
- 2006-08-07 US US11/500,735 patent/US7445768B2/en not_active Expired - Fee Related
- 2006-08-07 US US11/501,246 patent/US7510702B2/en not_active Expired - Fee Related
- 2006-08-22 US US11/507,986 patent/US7491047B2/en not_active Expired - Fee Related
- 2006-09-19 US US11/523,685 patent/US7507397B2/en not_active Expired - Fee Related
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2007
- 2007-01-09 US US11/621,397 patent/US7468179B2/en not_active Expired - Fee Related
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2008
- 2008-03-27 US US12/057,330 patent/US7988952B2/en not_active Expired - Fee Related
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2009
- 2009-03-27 US US12/413,339 patent/US8173107B2/en not_active Expired - Lifetime
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2010
- 2010-07-23 JP JP2010165688A patent/JP5629151B2/en not_active Expired - Lifetime
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2013
- 2013-08-19 BE BE2013C054C patent/BE2013C054I2/nl unknown
- 2013-08-19 FR FR13C0051C patent/FR13C0051I1/en active Active
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